Dating Advice: 8 Conversations Men Hate (and How to Make Having Them Easier)

If he hates talking about your ex-boyfriends

Generally, relationship expert Lisa Daily, author of Stop Getting Dumped, advises against opening the ex file when you’re dating someone new, but she says, “If you do bring up an ex, you should do it to highlight something bad about your ex or previous relationship that you’d like to avoid on this round, like, ‘My ex used to call me nasty names when he was mad—I’d never stay in a relationship where I was treated that way again.’”

If he hates talking about what you dislike about your body

The next time you’re feeling a little less supermodel-esque than you’d like, try rephrasing your insecurities. Telling your man, “I’m uncomfortable with how my tummy looks in this dress” instead of “I look so fat” can help him understand where you’re coming from and prevent arguments down the line.

If he hates talking about your future as a couple

“There’s never a fantastic time to bring this up,” says Daily, “But men want to be in relationships as much as we do.” She recommends sitting on the question until you’re three or four months into dating, then forgoing the expected “What are we?” for this approach: “Make it clear that you don’t sleep with anyone who’s not being monogamous to you,” she says. If he’s not on the same page, you’ll know instantly.

If he hates talking about his past relationships

“I was really into this cute girl,” says Andrew, 22, from Washington, D.C. “We went out on a couple dates that went really well. But then we had sex. Postcoitus, she asked me, ‘What’s your story?’ It’s a perfectly fair and reasonable thing to ask, but she asked it with an agenda of her own—she wanted to tell me her story. She’d just gotten out of a relationship and didn’t want any sort of attachment. But don’t tell me that after sex, after we’ve gone out, after I’ve let myself get attached. Either say it before the sex or let the relationship develop before dragging the skeletons from the closet.”

If he hates talking about his goals in life

Instead of asking him to tell you his five-year plan, Kyle, 24, from Philadelphia, says to open with something like, “What drives you to get out of bed in the morning?” He says finding out what your guy is passionate about in the big picture is the best approach because it’ll help you avoid making him insecure about where he is right this second.

If he hates talking about the reason he’s still single

“I’m not always comfortable answering questions about why my past relationships didn’t work out. Every relationship is different, and it’s not fair to be judged on what may have gone wrong in the past,” says Matt, 37, from Brooklyn, N.Y. If you really want to know, try turning the question into a compliment like, “You’re quite a catch—I can’t believe you’re single!” This puts the ball in his court and lets him spill what he’s comfortable with.

If he hates talking about moving in together

Know where your man stands on this issue in general before bringing up your specific situation, says Daily. She suggests mentioning a pair of friends who’ve moved in together to get his take on cohabitating. Then, “Don’t do any backhanded ‘Oh, my lease ran out’ moves. Have an actual discussion, not just a solution to an emergency.”

If he hates talking about marriage and kids

Don’t ambush him about the topic directly; instead, ask him about his hopes for the future. If he starts talking about where he sees himself a certain number of years down the line, you’ll find out whether starting a family is part of the equation. But keep in mind Daily’s warning about when to steer clear of prodding: “The worst time to bring up babies—and marriage for that matter—is at a wedding,” she says. “Guys are already feeling defensive and on guard.”